Hydrochloric Acid → 1-(4-Chlorophenyl)-5-cyano-1H-pyrazole-4-carboxylic acid

HRID 280458Notes

Reaction equation

HRID 280458 reaction equation
[OH-].[K+].[C:3]([C:5]1[N:9]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[N:8]=[CH:7][C:6]=1[C:17]([O:19]CC)=[O:18])#[N:4].O.Cl>C(O)C>[C:3]([C:5]1[N:9]([C:10]2[CH:11]=[CH:12][C:13]([Cl:16])=[CH:14][CH:15]=2)[N:8]=[CH:7][C:6]=1[C:17]([OH:19])=[O:18])#[N:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 13772949Ethyl 1-(4-chlorophenyl)-5-cyano-1H-pyrazole-4-carboxylate

Product 1

HCID 136541271-(4-Chlorophenyl)-5-cyano-1H-pyrazole-4-carboxylic acidYield 83.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A hot solution of 5.61 g of potassium hydroxide dissolved in 110 ml of 3A ethanol was added to a hot solution of 11.3 g of 5-cyano-1-(4-chlorophenyl)-1H-pyrazole-4-carboxylic acid, ethyl ester dissolved in 225 ml of 3A ethanol. The precipitated salt that was formed was dissolved into 1 liter of water and the solution was acidified with concentrated hydrochloric acid. The precipitated solid was collected by filtraton and recrystallized from toluene to provide 8.47 g of 5-cyano-1-(4-chlorophenyl)-1H-pyrazole-4-carboxylic acid. MP=192°-195° C.

Workup

  1. customThe precipitated salt that was formed
  2. customThe precipitated solid was collected by filtraton
  3. customrecrystallized from toluene

Sources & evidence

ORD record
ord-910ee7b93a1143f398614f811ad85168
Source dataset
uspto-grants-1986_05
Patent number
US04589905

Reaction notes

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